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Ben Horowitz: Why Hesitation is a CEO’s Worst Enemy

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Sep 12, 2025

Guest

Ben Horowitz

Ben Horowitz, Co-founder of the Silicon Valley venture capital firm Andreessen Horowitz and a bestselling author, shares invaluable insights on the psychology of leadership. He emphasizes that hesitation can be detrimental for CEOs and discusses how to embrace failure as a learning tool. The conversation touches on the founding story of Databricks, the controversial investment in Adam Neumann, and the current state of AI. Additionally, Ben highlights his dedication to supporting hip-hop pioneers through the Paid in Full Foundation.

01:35:38

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Episode notes

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ADVICE

Decide Even When Both Options Suck

Make decisive choices even when both options are bad because hesitation multiplies harm.
Lead by picking the slightly better path and committing so the company can move forward.

insights

INSIGHT

Success Is Many Small Hard Choices

Success is a chain of many small, hard decisions rather than one grand clever move.
Breaking sunk-cost paths and taking the next small right action compounds into outcomes.

volunteer_activism

ADVICE

Run Toward The Pain

Run toward problems instead of avoiding them; action often beats paralysis.
Prepare emotionally to have painful conversations because not acting usually causes worse outcomes.

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Honoring Hip-Hop's Pioneers

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Insights on Structure and Resilience

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Exploring Culture and Recent Discoveries

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Embracing Life's Unfairness and Learning from Music

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#18320

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The WEIRDest People in the World

Joseph Patrick Henrich

Korey Jackson

Joseph Henrich

In this book, Joseph Henrich explores how Western, Educated, Industrialized, Rich, and Democratic (WEIRD) populations developed their unique psychological profiles. He argues that changes in family structures, marriage, and religion, particularly influenced by the Roman Catholic Church, led to the emergence of WEIRD psychology. This psychology is characterized by individualism, self-obsession, control-orientation, nonconformity, and analytical thinking, which contrast with the more group-focused and shame-driven cultures of non-Western societies. Henrich uses research from anthropology, psychology, economics, and evolutionary biology to explain how these psychological differences contributed to the industrial revolution and the global expansion of Europe.

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What You Do Is Who You Are

Ben Horowitz

In this book, Ben Horowitz combines lessons from history and modern organizational practice to help executives build cultures that can endure both good and bad times. He highlights four models of leadership and culture-building: Toussaint Louverture, the Samurai, Genghis Khan, and Shaka Senghor. Horowitz connects these historical examples to modern case studies, including leaders from Netflix, Uber, and McDonald's, to provide practical advice on creating and sustaining a purposeful company culture.

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How to Be Free

Epictetus

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This book presents Epictetus's teachings on Stoicism, emphasizing that true freedom is a psychological and ethical achievement. It includes translations of the *Encheiridion* and selections from the *Discourses*, along with a glossary and introduction to Stoic philosophy. The book guides readers in managing emotions and handling life's challenges by focusing on what they can control.

#111

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The hard thing about hard things

building a business when there are no easy answers

Ben Horowitz

In this book, Ben Horowitz shares his personal and often humbling experiences in the tech industry to offer essential advice and practical wisdom. He addresses various hard decisions and challenges that business leaders face, such as firing friends, managing company culture, handling layoffs, and making tough strategic decisions. Horowitz emphasizes the importance of honesty, resilience, and adaptability in leadership, drawing from his experiences with companies like Loudcloud and Andreessen Horowitz.

In this conversation from Lenny’s Podcast, Ben Horowitz joins Lenny to discuss the psychological muscle every founder needs, why hesitation can be fatal for CEOs, when it’s time to replace a founder, and how to normalize failure while building confidence. They also explore the Databricks founding story, investing in Adam Neumann after WeWork, whether AI is in a bubble, where the real opportunities lie, and Ben’s work with the Paid in Full Foundation supporting hip-hop pioneers. The result is a candid look at leadership, product management, and what it takes to build enduring companies.

Timecodes:

00:00 Introduction

00:22 The Psychology of Leadership & Decision-Making

02:41 Leadership lessons from Shaka Senghor

07.56 Struggle, Pain, and Growth as a CEO

10:15 Running toward fear and why hesitation kills companies

19:35 Who shouldn’t start a company

22:36 The Databricks story: thinking bigger

24:54 Managerial leverage and CEO psychology

28:06 When founders should be replaced as CEOs

31:20 Normalizing failure for CEOs

37:57 Counterintuitive lessons about building companies

42:31 “Good Product Manager/Bad Product Manager”

48:21 Product managers as leaders

51:16 Why a16z invested in Adam Neumann after WeWork

56:23 Is AI in a bubble?

01:02:43 The biggest opportunities in AI

01:12:51 Why U.S. leadership in AI matters

01:18:53 The Paid in Full Foundation for hip-hop pioneers

01:23:18 Lightning round: book recommendations, products, and life mottos

Resources:

Find Ben on X: https://x.com/bhorowitz

Find Ben on LinkedIn: https://www.linkedin.com/in/behorowitz/

Watch more of Lenny’s Podcast: https://www.youtube.com/@LennysPodcast

Check out Lenny’s newsletter here: https://www.lennysnewsletter.com

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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.

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